The Quest for a Perfect Winter
by Adv4eternity
Summary: t's that time of the year again, and this time, May wants the holidays to be extra special. With the help of her friends, May tries to get closer to the love of her life. [Advanceshipping]


Time seemed to pass by quickly as three girls giggled in excitement. Sitting on the comforts of a cushy bed, a girl with brunette hair and an iconic bandana, blushed uncontrollably as her two friends were setting up a plan to make this a day to remember.

"May, with our brains and vision, you can bet that you will get together with Ash!" a girl with blue hair and a white snow cap exclaimed.

"And better yet, since it's snowing outside, you have more opportunities to spend time with him!" a girl with orange hair fashioned into a sideways ponytail added.

"Thanks, Dawn and Misty. I knew I could count on you two," May said, smiling.

The trio had met up to discuss strategies to bring May and her crush, Ash, together. In order to make this dream a reality, Dawn and Misty suggested that they would hide and observe the interactions between Ash and May, signaling May what to do and such. At first, May was skeptical of this idea, fearing that Ash would notice Dawn and Misty and therefore crush the plan, but because she was even more fearful that she would act like an idiot without guidance, she decided to accept the idea.

"So...when is Ash supposed to arrive?" asked Misty.

Just then, as if on cue, the doorbell rang. May sprang up from the bed, feeling her heart racing. She began to breathe heavily from nervousness.

"Oh no! I thought I was ready to do this, but now I'm having doubts!" May said shakily as she began to panic.

"Don't worry so much, May! Just open the door and get it over with! We got your back!" Dawn reassured May.

May nodded, then left her bedroom and rushed to the front door. Before she turned the door handle, she looked back to see that her two friends had taken their spots behind two pots of plants. After seeing a thumbs up and a wink from Dawn and Misty, respectively, May turned her attention back to the door. She slowly turned the handle and opened the door to reveal a cheerful boy, who was wearing a jacket and a baseball cap, covered in snow.

"Hey, May!" Ash exclaimed happily.

"Er-uh, hey, Ash!" May said, fumbling with her words. "Um, c-come right on in! You might catch a cold or something."

Ash nodded and stepped inside the building. As May closed the door behind them, she sighed and noticed how Dawn and Misty were smirking from behind the leaves of the plants.

"W-would you like me to take your jacket so I can hang it for you?" May asked Ash politely.

"No, thank you," Ash replied. "So, where's Max?"

"Shoot! I completely forgot about him! That brat could potentially ruin this holiday for me!" May thought to herself.

"Uhh, I don't know. So how about we-" May began to say, but unfortunately for her, her younger brother came running in to greet the guest.

"Hey, Ash! I didn't know you were coming!" Max said. "What brings you here?"

"Oh, hey there, Max! May invited me," Ash answered.

"Alright, well, instead of hanging out with my boring sister, how about you come show me all your cool Pok-"

"That's enough, Max," May interrupted as she pushes Max away. "Why don't you do me a favor and go tend to dad's Pokémon?"

"Okay! I'll leave so you can have fun trying to confess your lo-"

"MAX!" May screamed, hoping that somehow Ash didn't understand what her evil little brother was about to say.

"Hehe, see ya, sis," Max snickered as he runs towards the gym of the house.

Behind the plants, Dawn and Misty let out a sigh of relief. They both look at each other and understand that Max posed a huge threat to the success of Ash and May's getting together.

"If he comes back, we have to prevent him from ruining May's moment," Misty whispered to Dawn.

"If he does, let me handle the situation," Dawn whispered back, then returned her attention to the silent and awkward tension between Ash and May. Noticing how May were struggling to start a conversation, Dawn lightly tapped on the pot to catch May's attention. Fortunately, May turned towards the plants, while Ash looked around quizzically.

"What was that noise?" Ash wondered aloud. "May, is your house haunted?"

"Uh, no?" May replied, then focused on Dawn, seeing how she is mouthing to her to go outside with Ash. "A-Ash, do you want to go outside with me?"

"Sure. What are we going to do out there?"

"Ummm," May struggled to think up an activity or two. "we could...have a snowball fight or maybe build a snowman?"

May quickly glanced toward the plants to see a thumbs up from Dawn and how Misty was nodding in approval. This allowed May to relax, as she is happy she had not screwed herself over already.

"Sure, that sounds like fun!" Ash exclaimed. "It's a good thing I already have my jacket on."

"Yeah, give me a second to get my winter coat," May said as she enters a nearby closet. After finding a suitable jacket, and after finding her gloves, May walked back to Ash and opens the front door.

Upon stepping in the cold, May felt an immediate chill, prompting her to put on her hood and zip up her jacket all the way to close in as much heat as possible. Shivering, May looked towards Ash and noticed how he appeared to be completely content with the freezing temperatures.

Meanwhile, inside the house, Dawn and Misty brought the pots of plants to the windows that would allow them the best view of their friends as possible. From their position, they could see Ash and May walking toward the nearest open space.

"This really feels illegal, but I can't help but feel excited," Dawn said to Misty.

"Yeah, but I'd like to think that this is for a good cause," Misty responded, earning a nod.

On a large field, Ash and May trudged through many layers of snow towards the center. Just then, Ash tripped and fell on the ground.

"Ash!" May called out as she rushed towards him. Normally, she would see right through the intentions of the fall, especially since it seemed fake, but since she was so concerned for Ash's safety, she failed to prepare herself for a massive snowball that was coming her way.

"Gah!" May screamed in surprise before looking back at Ash to see him laughing.

"Ha! That was great! You should have seen yourself!" Ash exclaimed.

May appeared flustered from embarrassment, but in a matter of seconds, something in her head clicked, causing her to smirk.

"Oh, you think that was funny?" May said ominously, causing Ash to look at her worriedly. Suddenly, May charged towards Ash and tackled him onto the snowy ground. The two of them began to playfully wrestle, trying to push each other's head face first into the snow.

Off in the distance, Dawn and Misty were giggling in excitement, knowing full well that this would greatly boost the chance of getting Ash and May together. Behind the two girls, Max walked in after feeding his father's Pokemon. Suspicious as to why Ash and May were gone, and why Dawn and Misty were giggling to themselves behind two pots of plants against the window, Max walked towards another window and nearly vomited at the sight.

"What the heck?!" Max shouted, catching Dawn and Misty's attention. "That's gross! Why would Ash want to play with May like that?"

Before Max could continue to criticize Ash and May, Dawn swiftly grabbed Max and covered his mouth, preventing him from squirming and making any noise.

"Aren't you worried that you will choke him to death?" Misty asked.

"Don't worry, I'm only covering his mouth, so he can still breathe through his nose!" Dawn replied, while Max internally screams because he was afraid of catching the cooties.

On the snowy field, Ash and May continued to wrestle, oblivious about the amount of body contact they are doing. Running out of stamina, May finally submitted to Ash as he pinned her hands to the ground, looking down into her eyes. This interaction caused Dawn and Misty to squeal uncontrollably in the house.

Ash and May simply remain in the same position for a time, lost into the comfort and warmth of each other's eyes. And luckily for May, Ash's head was blocking the snow from falling onto her face, so she wouldn't have to squint as the sight before her. But before she knew it, May realized that Ash was beginning to get off of her.

"I win!" Ash cheerfully shouted, then offered a hand to May to pull her up. May accepted and blushed deeply from how close they have gotten.

When Ash turned around with his back facing May, May decided to seek revenge. She squatted down to scoop up a decent amount of snow, patted the snow into a round ball, then called out to Ash.

"Hey, Aaaash," May said in a singsong voice.

Ash turned around to see May chucking a snowball in his direction. However, because of May's limited movement in her thick, winter jacket, the snowball fell at Ash's feet. May groaned and braced herself after seeing Ash's grin.

"Oh, I see how it is," Ash says as he scooped up snow. "You want to play dirty, huh."

Ash chucked his own snowball at May, landing a direct hit. May wiped the snow off her face and pouts.

"But you also played dirty earlier!" May whined.

Ash shrugged and threw another snowball at May, hitting her face again.

"Ash Ketchum! You come right here this instant!" May shouted.

"Make me!"

May rushed after Ash, who had already begun to run away from her. The two of them ran around the field, and with each passing minute, it became apparent to May that she would never catch up to Ash.

Sensing that May was slowing down in their chase, Ash slowed down until May finally caught up to him. Ash grinned as May breathed heavily while walking up to him. May playfully slapped his arm repeatedly, prompting Ash to turn May around and hug her from behind in order to keep her from hitting him. May struggled to move but decided to submit to Ash again, enveloped by the warmth of his body.

The increasingly loud squeals of Dawn and Misty in the house alerted Ash and May, causing them to separate. May just then remembered that she was being speculated by her friends, so she looked towards the house to see toothy grins, and-

"What's this? Is that...Max?" May wondered as she squinted. Sure enough, she saw how Dawn had managed to suppress Max.

"Great job, you two," May mentally thanked her friends.

As for Ash, all he could see were two plants with a pair of eyes behind one of the pots, and two behind the other.

"That's so cool, May! I didn't know you decorated your plants with eyes!" Ash exclaimed.

May chuckled nervously. Then, looking up towards the sky, it suddenly occurred to her that the darkness was slowly creeping in, meaning that it was getting late. Not wanting to stay outside longer and risk the chance of getting sick, she decided that it was time for her and Ash to go inside.

"Ash, we should head in since it's getting late now," May said to Ash, who nodded in agreement.

From the windows, Dawn and Misty observed that Ash and May were making their way back to the house. Misty quickly brought the plant back to its original spot, while Dawn, with one arm holding onto Max, brought the plant back as well. Max, knowing that there was no use in fighting against Dawn's strength, simply walked along with her behind the pot to hide.

Ash and May entered through the door, the latter taking her jacket off and putting it back into the closet. Once again, the two stand silently, waiting for the other to suggest an activity or start a conversation. For May, her brain was constantly grinding, desperately thinking up something to save herself from this awkwardness.

Sensing that May was in need of help again, Misty turned to Dawn.

"I'm going to turn off the lights and change the temperature of the thermostat. This way, Ash will think that there is a power outage, and he and May will have to go to the fireplace to stay warm," Misty whispered.

"Great idea! Hopefully, they will end up huddling against each other because of the cold," Dawn whispered back, while Max squirmed in her arms to show his disbelief and disgust. Unfortunately for him, the two older girls did not care about his opinions.

Misty glanced towards the light switch and thermostat. Fortunately for her, they were located directly next to each other and were not too far away from her. She silently and slowly scooted herself and the plant in small increments as to not alert Ash. With only a few meters to cover, Misty reached the light switch and flicked it off, then quickly set the temperature to freezing.

Ash and May jumped in surprise, not expecting the lights to go off. Using the light of the conveniently already-lit fireplace, May's eyes dart around until they land on the suspicious plant that somehow repositioned itself next to the light switch and thermostat.

"Ahh, they probably want me and Ash to go to the fireplace," May realized.

"May, are you sure your house isn't haunted?" Ash asked, looking directly into her eyes.

"I'm positive. There must be a power outage because of the snow," May said.

"Ah, I guess you are right."

"Well, standing here won't be any good. Let's sit by the fireplace to warm ourselves," May suggested.

Ash and May situated themselves by the fire, holding out their hands to feel the comfort of the heat. May knew that the purpose of sitting by the fireplace was to create an opportunity to huddle with Ash, but, due to nervousness, she struggled to find the courage in inching closer to him.

Ash heard the sound of teeth chattering, so he looked at May. He noticed how she appeared to be lost in deep thought, staring straight into the he fire, and how she appeared to be shivering. Figuring out that the fire was not providing enough heat, he positioned himself closer to May and wrapped his arms around her. The action caught May off guard, snapping her out of her thoughts. She slowly looked to her side at Ash and saw how he was simply looking into the fire, so she watched the orange flames as well and relaxed. She snuggled into Ash's embrace, her head resting against his chest, and she slowly closed her eyes in content. All seemed to be going well, but the sounds of squealing interrupted the peace and tranquility that Ash and May were experiencing.

"I could have sworn that those weird noises were coming from those plants," Ash said, pointing towards the pots that were now situated against a wall, away from the light switch and thermostat. Ash stood up, much to May's disappointment, and walked towards the plants. Peering behind, he found Dawn, Misty, and Max, who was just released from the clutches of Dawn.

"Oh, hi there, everyone!" Ash said happily. "What were the three of you doing back here?"

Max was about to rat out Dawn and Misty, but a death stare from the former led him to keep his mouth shut.

"Well, we just arrived, but we saw how Max was tampering with the lights and the temperature of the house. We were just trying to get him prevent him from misbehaving," Dawn lied, punching Max's arm when he was about to deny these statements.

"Oh, so that's why! Max, why would you do those things?" Ash asked Max with a confused look.

"Hmph, you wouldn't believe me anyway," Max simply replied, crossing his arms.

After flipping on the light switch and setting the temperature back to normal, everyone settled down in the living room. May purposefully sat next to Ash on one couch and Dawn, Misty, and Max on another, although Max appeared very uncomfortable sitting next to Dawn. As they were having a light conversation about their plans for the future and each other's families, Misty decided that it is time to bring May and Ash together once and for all. As Ash and Dawn were busy talking to each other, Misty mouthed to May to pretend that she was still cold. Having an idea as to what is supposed to happen, May acted as if she was shivering. Soon enough, Ash noticed her behavior.

"May, is it still too cold for you?" Ash asked.

May nodded, so Ash decided to take off his jacket and wrap it around her body. Immediately, May felt a calm, soothing warmth of protection as she wore his jacket.

"Thank you so much, Ash," May smiled gratefully, staring straight into Ash's soft eyes.

"It's no problem at all," Ash said, finding himself to be lost in her gaze.

Since Ash and May were preoccupied with each other, Misty motioned for Dawn to "take care" of Max, while she fumbled around in a bag she brought for the final piece that would ensure that May's dreams would become a reality.

Dawn took the hint and swiftly grabbed Max, covering his mouth once again, and took him to a nearby closet. She quickly shoved him in and closed the door, using herself as a blockade so Max has no chance of escape. Meanwhile, Misty found what she was looking for: a mistletoe. She brought the plant to the kitchen and hung it above the refrigerator, then rushed back to Dawn's side.

"Sooner or later, they both will become hungry and rush to the fridge, where I hung the mistletoe," Misty whispered her plan to Dawn.

"That is so smart! Why didn't I think of something like that?" Dawn praised Misty.

In a matter of seconds, Ash and May's stomachs grumbled loudly, echoing throughout the house. Ash and May grinned at each other in embarrassment, then quickly ran to the kitchen in search of food. As planned, they attacked the fridge, looking around for any desirable treats.

"Hey, is that a mistletoe I see?" Misty nonchalantly asked loudly, then giggled quietly with Dawn.

Ash and May stopped their usual eating habits and looked up. There it was, the mistletoe. Upon seeing the plant, May blushed furiously, while Ash seemed confused.

"May, why is that plant causing your face to be so red?" Ash asked, "Is it possessed?"

"Well..." May took a deep breath, "...have you ever heard the tradition when it comes to mistletoes?"

Ash shook his head, unaware of such things.

"It's a tradition where if two people are found underneath one, they must...kiss," May said, becoming even more nervous and red in the face.

"Oh. So does that mean that..." Ash started to say.

"Yeah, it looks like we have to do the same here," May finished his thought.

This is the moment she had been waiting for for her whole life. Many days, months, years of fantasizing this moment would finally come true. Gulping, May stepped closer to Ash. Ash stepped closer to her as well. They both slowly leaned closer to each other. The distance between their lips closed steadily until they are an inch away. May began to feel a sort of small panic attack, suddenly losing the courage in continuing. But surprisingly, Ash was the one who sealed the deal, closing the distance and finally kissing May. May's eyes widened in surprise, then closed as she began to enjoy this very moment. All her doubts disappeared, and everything around her appeared insignificant compared to what she was doing right now with Ash. She did not want this moment to end, and frankly, based on how Ash still had not separated away from her, she knew he did not want it to end either.

Dawn and Misty cheered happily, hugging each other for May's success. Captivated by Ash and May's kiss, Dawn did not realize that she was stepping closer and closer to them, leaving the closet door unguarded. As a result, Max finally opened the door and ran out, relieved that he was no longer a prisoner to Dawn. However, after realizing what was happening, he was torn between whether he preferred his freedom or if he would rather stay locked up and never see a sight he would want to see. After seeing his sister and Ash that close to each other, he vomited.


End file.
